I'll try to answer these without references to religious figures or philosophical people to avoid incurring the wrath of some pseudo-intellectuals on this forum.
John Wooden - would love to pick his brain about basketball. Also, he's my inspiration as a teacher.
Richard Pryor - he's hilarious. Dinner with him would be a riot.
Tupac Shakur - overrated rapper, but underrated thinker and voice for the African American community.
Originally Posted by Bengt Ekerot
Interesting that no one has mentioned a female yet
haha, that is interesting. None made my list, either. Definitely didn't notice that trend. If we extend to Top 5, Margaret Bancroft might make my list. Top 20, maybe Hypatia, Ada Lovelace, and/or Beatrice Webb would make it.
I guess at the end of the day, I took this question very literally. Who I'd want to actually talk with, learn from, and hopefully have a good time with. I respect a lot of female historical figures, but I don't think dining with Elizabeth Stanton or Emma Goldman would be a good time.